My guest today is Stephen Gates, who is the SVP, omni-channel product design at WW (formerly Weight Watchers). In this episode, we discuss why Stephen likes to blend with locals while traveling, his favorite failure, why designers should build their own personal brand, accepting who you are, being authentic, motivation drivers, not believing your own hype, balancing your brand vs your employer's brand, aligning job opportunities with your personal brand, joining InVision, chasing opportunities over titles, dealing with failure, why not to hire fans and much more! For show notes, guest bio, and more, please visit: www.designmba.show Level Up Your Design Career (Free Email Course): https://levelup.designmba.show/
Stephen Gates is the SVP, Omni-channel product design at WW (formerly Weight Watchers). Previously, he was the Head Design Evangelist at InVision, working as a strategic partner to companies like Google, Amazon, The Home Depot, Bank of America, Facebook, Rolls Royce, American Express, Frog Design, WeWork, EY Partners, and many more to elevate the business impact of design through education, coaching, and thought leadership. His work has received over 150 international awards, his app design has been named as one of the World's 100 Greatest Apps, HOW Magazine named him #17 on the 100 of the most talented and influential creatives working today, Apple has featured his work in 10 keynotes and more.
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Jayneil Dalal: Today's amazing guest is Stephen Gates who is currently the Head Design Evangelist at InVision where he works as a strategic partner to 97 of the world's Fortune 100 brands to elevate the business impact of design through education, coaching, and thought leadership. He previously worked at McCann Ericsson, City and Starwood Hotels, building teams that created award-winning global advertising campaigns, multiple Fortune 100 brands and innovative digital experiences. His work has received over 150 international awards. His app design has been named one of the world's 100 greatest apps. How Magazine named him 17th on the 100 of the most talented influential creatives working today. Apple has featured his work in 10 keynotes and more. That is amazing. He shares what he has learned through his speaking engagements and The Crazy One Podcast which is an in-depth exploration of issues that matter to creative included.
Super excited to be talking to you, man. Thanks for taking the time to chat with me. I just want to ask you, man, you travel a lot, especially for work and your personal things. I got to ask you what is your favorite place that you've traveled to and if there was something that happened there that made it special for you.
Stephen Gates: It's interesting. I think it's always a little, you asked that question, it's like travel for what, right? Because there's travel for vacation, exploration, creativity. I mean, I think that the cities that I find myself going back to the most would probably be Barcelona and Paris. Barcelona has always been really, really interesting for me because, I think, when you go to a lot of other big cities, you go to London, you go to Paris, you go to things like that, you tend to see a lot of the same things that I would see here in New York but Spain is really interesting just because I think they tend to be a little more insular in their approach to things like you don't see them carrying French designer handbags, you see them carrying Spanish. And so, they tend to turn to themselves for more ideation. They tend to turn to themselves for more inspiration. And so, I think that whenever you look at, fashion, food, architecture, a lot of these things, it's developed very differently there for that reason. And I think also it has that great tradition. It has the Gaudi architecture. It has a lot of that sort of things. I mean, Barcelona is a city where everybody basically loves design and food. So, these are my people.
Jayneil: Wow! That is amazing. And I love the fact that when you're traveling to these places, you're actually noticing these small, small things. I feel that a lot of times when people are traveling for work or even just for personal pleasure, it's these small details that can kind of escape the human eye.
Stephen: Oh sure, but for me, I think the important thing is I always want to be a traveler, not a tourist because I think a tourist sees the same stuff that everybody else does. As a tourist, you want to travel and find what you have at home and just find it in a different place. I mean, for me, it's about how do you become a local as fast as you can. I don't want the spot that you think an American would want to go eat. I want the spot where you're going to go have dinner tonight because I think whenever you do that, you make a ton of friends, you find a lot of amazing experiences but you get a different perspective and, for me, that's what travel should be all about.
Jayneil: Wow! So, in your case, you're probably not going to want to stay in the same hotel that you stay in US. You probably want to maybe try out Airbnb or something unique where you can kind of blend in with the local people.
Stephen: Yeah. No, I’ve stayed in tons of Airbnbs now just for that reason because I had a CEO and it was one of the best pieces of advice I’ve ever gotten where he said “You don't really understand a country, you don't really understand a culture until you bought groceries there.” And I think that's sort of the great part about an Airbnb is like, yeah, I love to land on the ground, get settled, drop off my luggage but then like “Yeah, let's go hit the grocery store to get some supplies. Let's see what's good here.” Let's try and figure out if we can cook something.” Again, like I said, you want to try to become a local just as fast as you can.
Jayneil: That is phenomenal. I’m planning to go to Japan at the end of this month. So, I’m going to definitely take that advice and try to buy a local grocery there as soon as I land. I’ve always seen you as a person who is relentless about building one's brand. And what I wanted to ask you was what is your favorite failure that later set you up for success and then how that played in to you building up your brand in that process.
Stephen: It's an interesting question because if I’m going to be really honest, my brand was born out of failure probably because my origin when I started building my brand was because I got laid off and it was kind of like I was unprepared, I was unaware of what to do and kind of found myself in this moment of like I don't have a portfolio, my résumé is not in good shape. And so, I think it started out of this almost self-defensive position of failure, of this place of just sort of being uncertain and saying like “Look, I’m never going to be back in that place again” and I started by thinking “Well, yeah, I mean, important people have brands. They have websites. They stand on stages and they say things.” And I think it a lot of people, for me, think of brand as like a logo or like “This is my typeface.” That's not at all how I tend to think about brand. I think about brand the same way, whenever I actually design a brand, is what do you stand for, what are you known for. And in many cases, the thing that I found, as a part of my journey which is now why I kind of share it through the podcast and things like that is most people have no idea who they are or if they do, they have not made peace with that person. So, they try to be somebody else. They try to be overly generic. So, for me, that was what my brand was born out of was out of that moment. And I think it sort of evolved over time. I think it really found its voice whenever I kind of came into my own and realized that I cared about what other people thought for way too long. If you know anything about me, I’ve got tattoos on both of my forearms, the one that most people know. I have “here's to the crazy ones” tattooed on my right forearm. It was such a crisis to me and the realization was so strong that I actually tattooed my body to remind myself to never go back to that place of giving other people that much power. And so, I think, that became whatever my brand found its strength and its voice was in the realization that I was so not alone in that journey and that the failures that I’d had, other people had had and that the only reason why I didn't know that was because I didn't talk to people or the other people really wouldn't talk about the problems that they had. That's why I said it started, honestly, in a very selfish place but then evolved into really embracing that kind of like sharing is power and that whenever I do that, that is a very different version and probably the most authentic version of any brand because it's authentically me.
Jayneil: Your work has been featured in multiple Apple keynotes and given the upper echelons that you ever attained, somebody would assume that “Okay, now, Stephen can just like kick back and relax” but I see the opposite like I see you even hustling even more than that. So, what is it that keeps driving you even now, the fact that your name is pretty popular in the design circle and even beyond that?
Stephen: I mean, look, the stuff with Apple and the awards I won and stuff are great. I mean, I still look at my portfolio and see what could have been better. And I think that's always the thing is no matter where anybody is, no matter where they are in their journey, no matter where they are in their career, I think, the moment you believe the hype is the moment you're irrelevant. One of my best friends always has this line where it's like “You need to hustle until you no longer need to introduce yourself.” I think, for me, it can always be better. I think there's always something new. And I get these people who will come to me and say like “Look, I’m trying to figure out if my best work is behind me.” That's totally up to you right and I think, for me, if you show up every single day and you hustle like you haven't made it. I mean, again, I look at the world and I see there are so many people who do it better than me, who do things that are better and that I wish I could do be more like that it drives you. And I think it is just committing and being unafraid to do that work.
Jayneil: Wow! So, then you're in a situation where you're always relentless about building your brand and then you're also working for InVision, so you've got the company's goal. So, then I’m trying to figure out like how does a person like you align their personal brand-building goals along with the company goals so this way there's no conflict but you still get to do what you want to do.
Stephen: I think it's advantageous but it's tricky at the same time right because it absolutely is a balance and, I think, whenever I show up to do a talk, whenever I show up to do something like that, I’m showing up as a member of InVision who just happens to then have a podcast. And I think it needs to be very clear that that is the order because, I think, the moment it becomes all about you and it's just about your brand, whenever it's just about you talking about yourself, then you tip too far to the egotistical side. And I think there's always this push and pull that we're all dealing with. I think, on the one hand, absolutely, you need to show up, you need to be a member of your team, you need to invest in what that is wholeheartedly to be successful but I think if you lose yourself too completely on that side, again, if you don't know who you are, if you don't have a brand, if you don't know what makes you different, then I think you struggle in your current job because you can't really articulate what it is you want, you can't really articulate where it is you want to go and I think there's this weird trap where the job you're in right now wants the “we”, they want you as part of the team as well they should but, I think, your next job wants to know what did you do as an individual, what did you do as things like that. So, for me, I’ve also found it to be incredibly liberating because companies know exactly what they're getting. I mean, I’ve got 80+ hours on a podcast, I do talks, I do write. It’s really, really clear and, I think, just like any brand, you can look at a brand and say “Yeah, you know what, that's for me. I really like what they stand for. I really connect with that” or “You know what, I’m not really feeling that. I don't really think that that's what's going to be good.” And so, for me, it's been great because the brands who look at me and kind of go like “Yeah, you know what, that's not what it is that we really want,” I don't have to go through the exploration of saying like “Hey, would they be really good to work with?” And I think that was, for me, why I made the change to go to InVision. I mean, it's the first time in my career where I don't have a designer or head of design or creative director or something in the title where it's much more about coaching and teaching and thought leadership because, I think, they came to me and I had a conversation with Clark from InVision, the guy behind the emails was actually real, where he just said “Look, where do you think there's an opportunity? What's your passion?” And whenever we talked about it, he said “Great. Can you write a job description to do that?” And I think that's the mark of a great company and of great leadership is that they hire smart people and then they do this crazy thing of actually trusting them to do what they do well.
Jayneil: I just want to circle back to the point where you mentioned that too many people just don't know what the brand is and then in the process of that, they just take whatever opportunities that come their way. So, I want you to elaborate on that because I see a lot of designers, when we meet at conferences and stuff, a lot of them are just happy just getting that brand name company on their résumé but then there's no other end game or some kind of goal. Why should the designer even bother building their brand? That's what I’m trying to get at.
Stephen: That's why I said, for me, it's not about just investing in a logo. It's investing and understanding who you are because, I think, one, if you want to be successful in your current job and advance, you need to know that. If you want to advance from an individual contributor to a team to leadership, you need to understand that but, I think, in many cases, it really is about are you clear about what matters. Two of the interview questions that I’ll ask people is I’ll ask them like “Can you tell me how you have an idea?” because I’m trying to figure out their level of self-awareness to their process but also “Can you tell me what you need to be happy?” because, I think, in any relationship, you need to show up as an individual, you need to show up as a person that will say “These things matter to me” because whenever you don't, and I think you're right, I see far too many people in this industry who think that where you worked and where you went to school is who you are, I would violently disagree. I think that is not the case at all. I think that's why I see so many résumés and get so frustrated whenever you see a résumé and that's all it is. It's like “Here's where I went to school and here's where I worked.” That tells me nothing about you. It tells me nothing about what matters to you, why are you different. This is your first introduction to a company, to a leader. You would never start a conversation that way in real life. You don't go to a conference and go “Hi, my name is Stephen. This is where I went to school and this is where I worked.” So, why would you do it there. And I think that's why, for me, the brand is important because I think most creatives that I see have spent almost no time thinking about what matters to them, thinking about what they want to be happy, thinking about what their goals are going to be and finding clarity in that but, as opposed to that, what they do is they say “Well, I’m not happy here. Let me go see what the industry will give me.” My approach has always been “This is what I want. Let me see what I can go get that aligns with that.” So, it's a fundamental shift and I think that's what the brand will give you the clarity and focus to let that happen.
Jayneil: So, when you were in the process of joining InVision, I’m sure, you probably were evaluating other opportunities. So, I want to actually try to take a deep dive into your head like what mental models were you evaluating to kind of see that “Okay, I am probably going to be reporting up to Clark or somebody on his team or working with them and I want to make sure that these are the bosses that I work for that I get inspired by them.” So, without naming the other people that you turned out, I’m just kind of trying to get into like what were the characteristics that made you feel like “Okay, this opportunity, probably no and probably yes with InVision.”
Stephen: Yeah, for me, it starts with the company and its values, probably even more than the people because the thing that I’ve learned and I think even the hard way a few times, people leave. I mean, I’ve gone to work for companies because I love the CEO and I love the CMO that I was reporting to and within six months they were both gone and then you're sort of stuck with a company in a position that without those people feels very different. So, I think a lot of it, for me, was looking at I loved the risk that they were taking and saying “Look, we want to be the world's largest fully remote company. We have no office.” I loved that. I loved that we could say “Look, we don't care where you live in the world. We just want the best talent.” I think there was a lot of those sort of values and decision making and the ability to tangibly and really put your money where your mouth is that matters. And I think that's always been the thing that I’ve tried to evaluate in my career. And I think that was why I turned down a lot of the other companies was because, for me, there was a real struggle about “You know, great. I want to go into another company. I’m going to be the chief or head” whatever and “How am I not back in this position where I’m at today in three or four years of coming into a company that says they want to do all these things but whenever push comes to shove, they seem to lack the ability to kind of walk their talk.” And so, that was a big evaluator for me. And I think that's also why, in a lot of ways, my career path has never made sense because, for me, it's always been much more about the opportunity. I mean, I was working for McCann, an ad agency, and decided to go work at Starwood and everybody was like, this was 15 years ago, “Why on earth would you go in-house? Why on earth would you go to some hotel company?” And I think I spent three years with all my friends kind of joking and saying like “Well, hey, are you ready to come back to where the “real work” is?” And then about year three when we showed up in that first Apple keynote, then all those same people wanted to know if I was hiring. So, again, that's why I’ve gone from an agency to a hotel company to a bank to now a SaaS company is because it's much more about the opportunity and the beliefs where I feel like I can be successful as opposed to chasing a title or a company or a salary because I think those things all, at the end of the day, are fine but they're transient and they aren't going to set you up for real success.
Jayneil: Somebody might look at you and say that “All right, Stephen’s already figured it out. He's got amazing following on Twitter. He's got his own podcast that's trending on multiple categories on iTunes and other platforms” but there must have been a point, Stephen, where honestly you were starting out and you were nobody before you became a somebody. So, what was that phase like? And I’m sure even at this level you must face a rejection in certain things that you want to do. So, I wanted to kind of like drill into those two aspects like what does rejection look like for Stephen at this level first.
Stephen: I mean, I kind of have to laugh whenever you even kind of talk about it that way because rejection, for me, is the exact same as everybody else. I mean, honestly, I think that, for me, is the interesting part in all this is that it's not that different. And I think you look at the result of what I’ve done or the work I’ve done or starting the podcast, all that sort of stuff, it's the result of a very lengthy journey and a whole lot of failures to get things wrong but it was just simply my ability or my willingness to let it fly to then see how was this going to work out. I mean, I started a podcast which was I felt like there was some things that the world wasn't talking about. I invested 150 dollars in a microphone and, honestly, to this day, basically, sit and talk to myself in my home studio and then put it out into the world because I think if you go into it to saying “Look, I want to be known,” if you go into it to say “Look, I want to be famous. I want to be rich” or whatever it is, you're never going to be any of those things. I think if you do it because you love it, I think if you do it because it is authentic, I think if you're willing to put the work into it, then those things come but no, I mean, you launch the podcast, nobody listens to it and you got to keep grinding on it, figuring out how to make it better. Again, I’ve spent no marketing dollars on it. And that's why I said a lot of it, for me, was … Because I’ll be honest. When I look at my career, I think there are so many more people out there that are so much more creative. I think my superpower is I’m just willing to work harder.
Jayneil: Can you share a story, it could be recent, it could be in the past, where you faced a rejection that you thought was big and just how you overcome that? Because we see a lot of stories about you doing so many great things. I just want to kind of like go into a place where Stephen also faced rejection and then what was your process getting out of that and overcoming that.
Stephen: I mean, obviously, for me, the biggest one was probably my exit from Starwood. I got laid off. A lot of people won't say that like “I got an exit” or “I got packaged up” or “I decided to leave.” That wasn't the case. I got laid off. I had an amazing, amazing CEO who I dearly loved. I had a team that was kind of my heart and we were doing such great work. The board decided to push the CEO and the CMO out and then decided that I was a very visible remnant of that last regime and they wanted to sell the company. So, it was going to be better for them to lay me off I. mean, I got laid off with my work running globally in an app commercial after four consecutive keynotes where we were the featured app. I mean, I couldn't have performed any better. And I think a lot of it, for me, is that those moments have taught me that failures are bigger or smaller. And that was a devastating one because it was not my decision to leave, it was not my decision to walk away. It was taken from me. And it's heartbreaking right but, I think, whenever those moments happen, the thing that you start to realize or the thing that I realized is I need those moments. I almost need to force them. I need to push myself to the place where maybe I’m not getting laid off but then I’m doing something wrong, I’m doing something where I’m learning because, I think, confidence and expertise comes out of failure, which sounds so backwards to so many people but that's the thing. If I go out and just do the same thing all the time and the danger in creativity is that I’m just going to go out and do what I’m comfortable with, I don't build any confidence, I don't build any expertise. I just sort of repeat the same thing over and over again. I mean, that was a case where I’d sort of, whatever had happened, I posted this sort of very melancholy thing on Facebook and feeling sorry for myself and being really heartbroken about that. And I think it also is important to have a support system that will help build you up. And I think I had one of my friends called me up and candidly he was just like “What the hell is wrong with you?” And I’m like “What?” He's like “You're going to go take that post down right now.” He's like “Yeah, you got laid off. Yeah, it's going to hurt and do all that stuff” but he's like “Look, you do not feel sorry for yourself. This does not affect who you are.” And I think that there are some of those times when you need to be able to fall down, you need to be able to get it wrong but I think you need to be able to … because, for me, it's only a failure if you don't learn from it. And I think that's why there are a few words that I have an allergy to. ‘Failure’ is one of them because failure means I did something wrong and I didn't learn from it so that it is a finite end state where something went really bad. Failure is just badly positioned learning. And I think, that's my thing. So, for me, it's my ability to go out to test it, to push the boundaries, to stand on bigger stages, to take on tougher topics because I’m going to learn from it. I mean, look, there are people who say I’m a great leader and people who think I’ve done amazing work. There are people who have worked for me, I’m sure, will tell you I’m an absolutely horrible leader that, I’m completely full of it, that they don't like that style at all. So, it's not just like this thing where it's just champagne and puppies all the time but I think it's how you look at that to the point where you're trying to go out to almost seek it out because that’s what I said, I try stuff all the time and you're saying like “Well, that didn't work. Let's not do that again.”
Jayneil: So, what are some of the new things you're trying to do these days in terms of exploring new things and just going back to stuff you said about like you always want to put yourself in a position where you're in a spot where you don't know what the answer is but then it forces you to learn? So, what are some of the things that Stephen is doing these days to just push himself out of the comfort zone?
Stephen: I mean, the job with InVision was definitely a big one because we work with 100% of the world's Fortune 100 brands. That means that I’m going in shoulder to shoulder working alongside a lot of the world's most creative and best design leaders. So, I think, if you really want to put yourself to the test to be able to see “Do I really understand what I’m talking about? How am I as a coach? How am I as a teacher? How am I as a thought leader?”, this has been a daily exercise in looking at getting out of because, I mean, for me, design was a very, very comfortable space. I know how to go in. I know how to design product. I know how to do innovative work and be able to get that to go out the door. I wanted to look at the leadership piece. I wanted to look at those sorts of things. I think a lot of it then inside of that is also, for me, how do I help really trigger conversations that I feel like we need to be having that we aren't really being open enough about. The fact that every single company is dysfunctional but we all sort of pretend that everything is great, I believe, that every creative quietly kind of feels broken inside but we all put on this mask and go on social media and talk about how amazing everything is. I feel like we're in this moment of a maturation of an industry that is colliding with this sort of, I don’t know what, like social surrogacy where it'd be great if for Halloween, we all went as we pretended to be on social media. So, for me, it's the ability to go out and explore these topics and try to push the industry on it to be able to do those sort of things because, I think, for me, it forces me to go to learn to lean in, to invest, to figure out how do we work on this stuff, that it's not just showing up and saying “Hey, there's a problem.” Anybody can do that. Again, I think, for me, it was just wanting to even holistically push myself into a completely different space untethered to what I’ve done before. I mean, that's the biggest one recently.
Jayneil: Wow! I’ve noticed that after attending some of your talks, man, it is really hard to get a hold of you. So, I guess what I’m trying to figure out now is how does one ask for a favor from someone as busy as you without seeming too clingy or needy, I’m not sure what exactly the word is, just in terms of reaching out. And I’m sure there are a lot of people trying to get a hold of your time, trying to schedule stuff for you. So, what I’m trying to figure out is how does one come across as genuine, at the same time not too clingy like “Oh, he's always sending me emails or requests” and things like that.
Stephen: I mean, what I would say is there's no substitute for being genuine. I think that the easiest way to get a hold of me is social media. I’m on Twitter, I’m on Instagram, I’m on LinkedIn. You can email me through my site. I try to get back to everybody as quickly as I can. My travel schedule sometimes interferes with that a bit. The people who I want to help, the people who I always make time for are the ones who show up and are honest. If you want me to endorse something that I’ve never been to, if you want me to give you a quote about a book I’ve never read, I’m not doing that. I’m not going to put my name to something I don't understand but for everybody who reaches out with a problem, everybody who has something they want to work on, I’ll find the time to get back to them but I think it's also really good if you reach out to me or anybody, if you're looking for a mentor, just looking for advice, be clear about what is the value exchange because, I think, for me, if it's just like “Hey, I’d love to sit down and have a cup of coffee with you,” I don't understand why should I invest my time in that right. If it's just “Hey, sit around and say something coo for half an hour,” that gets very hard for me to find time for just that in my schedule. If it's like “Look, this is the problem I’m having at my company. This is the thing I’m trying to work on. This is what it is that I’ve done and it's not working,” then it's very clear what the discussion is, it's very clear if I can help or not, is a 30-minute cup of coffee enough to be able to do that or is this something different. Like I said, there's no substitute for being honest and being genuine, being vulnerable whenever you do that and, like I said, just be clear about what is it that you're looking for because, I think, when you're able to do that, you'll be amazed at how many people will reach back out and want to help.
Jayneil: So, when you say the value exchange, does that mean that if I’m reaching out to you or anybody for that matter, it means what is it in for the person that's mentoring me or in the sense that what is it that exactly I’m looking for because what if I don't have any value to provide in return?
Stephen: That's what I’m saying. Even in a mentoring or a conversation, I think the value exchange is if you show up and say “Look, I’m struggling with this. This is what it is that I need advice on,” then I understand the value that I can provide to that conversation. And I think that then is a clear value exchange. And by value exchange I don't mean “What do I get out of it and what do you get out of it?” I think that it's just what are we getting together for like at the end of this, what is success going to be. Just like any project, just like any creative endeavor, at the end of 30 minutes, an hour, whatever that is, what is success going to be so that I can figure out can I deliver that, is that really the right format for it, does it really need to be in person or is that something we can do over email. That's what I said. We're very clear about what both sides are looking for.
Jayneil: And then going back to the point where you mentioned that you actually look at people and try to figure out if they are honest or genuine, I’m trying to figure out how do you read people. I know briefly there was a point where you had mentioned that in our previous conversation that you actually have some friends at the FBI, if I’m not mistaken, or you've read books on it. So, I’m kind of curious about that because you meet a lot of people. So, how does that process go about reading people because I’m sure people want to get better at it?
Stephen: Yeah, I’ve studied with poker players and FBI agents and other things like that about how you do some of the [inaudible] for that. I think we all know if somebody's being honest. I think if it's just simply like “Hey, I want to do this for me” or “I want you to be able to do something. I want you to be a trophy” or “I just want a photo” or whatever, that's fine and there are moments for that but a lot of it, for me, is what I said, how vulnerable are they willing to be, how much time are they willing to invest in this, are they willing to be able to do any work to be able to change things because if it's just like “Hey, look, I just want to get together and complain to you about how things aren't working for me,” that's what I said is, I think, that's fine but like go do that with your friends or go do that with something different because, for me, the conversation I want to have is that someone is struggling with something and they just simply can't figure what the road forward is and then whenever we talk about that, they are willing to put in the work and to be able to do that. And that's why I said it's not an absolute process. It's not like you get it right 100% of the time” or do things like that. I mean, I’m a huge believer in also just saying yes to a lot of stuff. I think I’ve been able to travel the world and gotten to work with some crazy clients because I just said yes to go trying to do something. That's what I’m saying is, I think, it's about people who want to show up and have a conversation. If you just want to do fan worship or things like that, it's strange to me, I’ll be honest. If it's just like “Hey, I want to tell you how great you are,” that's great and it's wonderful and I’m so humbled and appreciative. I wouldn’t just have this thing like I’ll never hire somebody who's a fan of mine on my team because I need people who can have a conversation, I need people who can push back, I need people who can show up as themselves. That's what I said is, I think, you can tell if somebody's showing up and really being honest about those sorts of things or has a real problem. And that doesn't matter your seniority, it doesn't matter how long you've been in the industry. None of that stuff matters. It's just kind of, again, are you willing to just kind of show up and want to have a real conversation.
Jayneil: A lot of times there might be a hidden agenda when someone shows up and wants to meet you, they might want to work with you in the future or something like that but then there is this train of thought that, I think, is not about just who you know but who knows you. So, they might just want to put themselves out there like “All right, Stephen’s going to be there. I’m just going to put myself out there” but they may not have that amazing product design, they may not have that amazing website or portfolio design. So, is that okay to just put yourself out there in the radar of other people to at least be visible that “Yeah, at least Stephen knows me now” or at least you got to know me even though I didn't ask for anything.
Stephen: That's what I’m saying. I think that's the difference. If the reason why you go into that interaction is because you want to post on social media that we talked or something like that, I don't think that's going to be an interaction that probably is going to yield a whole lot of value because if that's all you're going into it for is to be able to say like “Well, now we're friends” or whatever that is, one, it's not genuine; two, it puts me in a very weird place of kind of like “Okay, do I just let it go? Do I have to kind of correct it?” because the other thing is, and I think a lot of people don't think about this, if somebody comes to me and says “Oh, you're friends with so and so. I saw them post that you're friends or you hang out,” like I said, I’m always going to be honest. And so, in that moment I’m going to correct it and say “Nom actually we just hung out once and they took a photo.” So, I think a lot of it is also just sort of understanding the moment versus your career and who you are and doing those sorts of things. That's what I said. If somebody wants to come because there's a problem that they've had, if they want to come and talk to me about something that the show helped them get through, I’ll make as much time as I can for that every single time. I don't care what their portfolio looks like. I don't care where they work. I don't care about any of that stuff. I’m not somebody that's like “Oh, unless you work at these big companies, I’m not going to talk to you.” It's never been that. It's more just how do you show up as a person and be able to show up to do that because, like I said, I think, if you're trying to fake the funk and try to make yourself into something you're not, people are going to find out real quick.
Jayneil: And then how do you go about nurturing your connections. You all have a lot of powerful people in your network, if I may. I’m just thinking about Scott Belsky and a bunch of other people. So, I’m thinking about it as like as you're busy in your own ways and they're busy in their own ways, how do you reach out to them or how do you connect with them or, I guess, how do you stay in touch or is it the experiences that you have had with them that means that you don't need to keep doing that game of keeping up with them?
Stephen: Well, I think, it's sort of all of the above but I think more than anything they're people. I think the problem is, and I think LinkedIn and a bunch of other things don't help with this where I think that sometimes people will look at them almost like they're trading cards like “I need to collect all these people and then I’m important.” I mean, I am friends with who I am because I think I try to show up and talk to them and treat them like a person. I understand how many kids they have. I understand where they live. I understand what they're going through in their lives and what's going on with their marriage. There's a lot of things like that. I mean, they're people. And I think whenever you're able to do that and, again, you show up genuinely, you invest in who they are, you reach out to them, you have something in common, you tend to be able to make friends with a whole lot of people because that's what I said, if you just kind of show up and it's like “Oh, you work at,” I don't know what, Apple, Google, wherever, “That's so impressive. I want to know you because you work there,” again, that's not an honest way to show up to people but a lot of it also, for me, is over the course of my career, a lot of those people weren't who they are now whenever I met them. I mean, I first met Scott when I was a beta tester in Behance, way back before Adobe bought them way back whenever they were just kind of like this small little startup and before Scott wrote Making Ideas Happen and all that stuff and I was just so impressed and so enamored with his thinking and watching his stage presence and I was like “Man!” and I just went up like I do with a lot of people, I’m just like “Look, I love your talk. I’m a fan.” And that's what I said, anything based on that then just sort of having that conversation. And whenever we're around each other or do stuff like that, we can say hi and catch up but I think, that's what I said, they're people. And I think whenever you kind of invest in them the way you invest in any relationship and your life, then you tend to have a good network but I think also then you have a sincere network. There are a lot of people who want to connect with me on LinkedIn or follow me on social media just so, again, they can say that I’m in their network. I don't know who they are. For me, the people that I value are the ones where it's like, yeah, if you want to ask them about me, they have a story, they have something real to say like there's a real connection there, not just some connection in the digital ether that doesn't really mean anything.
Jayneil: That's an amazing story, man. I’m trying to figure out this thing where you're in this position as the head design evangelist at InVision where you're meeting so many different clients and people within the company know that and they also know that you're building your brand. So, I’m trying to figure out that how does one in a position like you also continue to strive for your career at the same time and not alienate your peers. Let me try to explain that question with a better example. So, a lot of times people might be jealous of their own peers just because they're doing better, they're absorbed with what they want to do, they're goal focused and I’m sure you have your own goals but how do you take the time to still connect with the peers where when you get to the finish line, it's like people are cheering for you, not like one of those people where they get to the finish line, they have all the success but, honestly, nobody gives a shit about them? And this goes back to this point where if Mahatma Gandhi was paid a billion dollars, I don't think anybody would like flinch an eye, but then if somebody else in his position was given that much money, they would be like “No, that person's XYZ.”
Stephen: I mean, again, I think a lot of it, for me, goes back to how do you show up for those other people. And that's what I said, I think, for me, it's working for a company first, my brand is second. I do the podcast on my own time. Again, I think my brand has given me the ability to be able to do a lot of things but I think it's also for your peers, show up and genuinely support them or ask what it is they're doing, ask them to work on what it is that you're doing, invest in who they are and invest in those things because, that's what I said is I think if it is a human-to-human connection, you tend to relate to people very differently as opposed to if it is a political battle. And that's what I said, I mean, I genuinely want to root for other people to be successful. I genuinely want to invest in that. I think you can't fake that and you know if people are feeling that way or not. And I think if you can sort of show up in that way, if you can invest in other people genuinely, if you know that they're going through a tough time in their life, text them and say “Hey, look, how's it going?” You want to jump on a call, again, just the same way you would with anybody else. Then your professional life becomes an extension of who you are as opposed to “Hey, I have this persona in my professional life which does not align to who I actually am.” And I think that's the problem. It's interesting whenever people do intros for me or whenever people talk about me, it strikes me as so strange that they will describe me as honest and that what you see on stage is who I am in person. The fact that those things are different means that a lot of us have real problems in our social relationships. If honesty is something that is different, that's a problem. Again, we're all pretending to be somebody else at work and that's not who we actually are. People know because, I think, so much of this entire industry, so much of success comes down to just trust and you can't fake that like “Do I trust this person to work with them? Do I trust them to support them? Do I trust that they are being honest?” because I think that's the thing is they're only going to support you, they're only going to be able to do those sorts of things and be able to rally behind you if they trust you and feel like what you're doing is genuine because if they don't, then that is that thing where it's just kind of like, yeah, if they trust you, great, let them be successful, pay Gandhi like a million dollar or whatever it is but if they don't, then it's kind of like “He's faking that” and, I think, that's the point where they look at it and go like “You know what, I have a problem with him getting that success because who he is on stage or who he is in that job is not who he actually is” or “That's not the way she is whenever she's you something else.” And so, I think there's that just sort of underlying issue of trust. And I think if people really trust you and if you're genuine, then they'll always kind of come to your aid and really be your cheerleader.
Jayneil: So, then this is kind of a caveat of that discussion is you probably have to work with a lot of people who may not be on the same playing field, as you know. What I mean by that is they may not have the same level of motivation and hustle and some things might be clear to you like “All right, this is the level I’m operating at.” So, how do you try to have empathy in that situation?
Stephen: Empathy, I think, in a situation like that means that you almost kind of feel sorry for them or they're doing something wrong. For me, it's just more about how do you show up in that moment to be able to give them feedback probably and to be able to coach them on what are they going through, what do they want to do differently, how do they show up as their authentic self to raise their game to be able to get better results and to understand that they're going to do it in their way not in your way. Again, there's sort of an arrogance there like “I work this way and I do things. So, this is the way everybody should do it.” That's not the way creativity works but I think you constantly work with people with different skill sets but it's showing up, again, with a respect, with a humility, with an understanding that that's where they are and tools that they bring to the table and to look at those and respect them and understand what they are and then kind of say “Okay, look, there are areas where …” because I’m sure they look at me and think “Hey, there's some stuff that he could do better.” So, that way, I think there's always a good value exchange there between “How can I help them? How can they help me?” because everybody, everybody has something that they can teach you. It's just that do you have the humility and the ability to actually listen.
Jayneil: So, now, I’m thinking about if you have to … it sounds like a cliché question but there are probably so many young designers or junior designers starting out in this field. So, I guess, if you have any words of wisdom for them? And if there's any specific call to action they can take today, what would that be?
Stephen: I think the advice that I’d give to them the most is you need to understand the cycle that you're going to go through. Especially, it's understanding that creativity is going to be the real value that you're going to bring to this industry and your career, not design, not copyrighting, not coding, not whatever that is, because, for me, the thing that's going to drive real value is going to be your creative process, your perspective, what makes you different. And so, kind of like what we talked about before, taking the time to start to understand how do you have an idea, what makes you different, how do you do those sort of things and to be able to try to start to work to make peace with them, I think, is incredibly important but also understand that you're going to go through this process. In many cases, whenever you do anything creative, you'll start by copying other people right. It's how we all sort of learn. And then you'll start to be able to work out from that or then you start to develop your voice, you develop a full-fledged voice and it's making sure that, like I said, you're leaning into what is that voice, what is that differentiator but I think that it's also knowing that that self-awareness because it's incredibly important because the wall that I watch most creatives slam into is whenever you hit that inflection point of going from “I’m a designer, I’m a copywriter,” whatever it is “And all of a sudden, I’m being asked to be in a leadership position” because the other challenge with, I think, leadership is that all the skills you have developed up until that point probably don't mean much of anything whenever it comes to leadership because execution is about “How do I understand the tools that I use? How do I understand the challenge? How do I have ideas? How do I do a lot of those things that are very execution focused?” And then whenever we get into leadership, suddenly it's about sociology and psychology and social engineering and inspiration and it's just a holistically different skill set. And I think, that's why whenever you're able to have that self-awareness to be able to say “Oh, well, this is what I struggled with” or “This is the thing that I went through” or “Yeah, I can empathize with where you're at because I went through something similar like that and this is what I did,” the ability to start to have those tools, I think, will get you into leadership and successful leadership positions much, much sooner than if your creativity and your process is just happenstance. So, I think, that, for me, is sort of the thing is that where you go from looking to that external inspiration to looking to the internal inspiration, it really is figuring out how do you make peace with yourself and how do you understand that your story is never going to be like anybody else. You're never going to find somebody that grew up the way that you did, they went to the same school that you did, that had the same struggles that you did, whatever that is. And I think, for most people, whenever they think about that and they think about it feels like you are very different that you are very alone and normally whenever that happens, the difference is bad. My argument is I would say the difference is good because that's what makes you different, it's what makes you stronger, it's what makes you unique which is what this industry wants and needs is just your ability to lean into that and accept it. So, I think that, most of the time, is the advice that I’ll give to kind of designers who are starting out is that that doubt is natural and it's starting to look at that, embrace it and trying to figure out how does it define you and how can you use that to your advantage.
Jayneil: And would it be fair to say that the way you made peace with your own creativity and who you are came through trial and error and years of experience or at what point you could say that “I just have made peace with this is who I am, this is Stephen Gates and this is what I am. This is my brand?”
Stephen: On the one hand, I would say I don't think that process is ever finished. I think I’ve had increasing levels of embracing it. There's no way to talk about this without sounding like some kind of weird humble brag. I mean, for me, the breakthrough moment did come whenever I did a lot of work with Apple because I found a company that I respected so much and I thought did such great work that all the things that I felt made me different, all the things that I always questioned, all the things that everybody didn't understand or said was crazy were suddenly embraced there, suddenly made me very, very successful in the work that I did there and it made me really re-evaluate why was I giving everybody else so much power in controlling the way that I looked at myself. And so, it was something I struggled with for a long time and I think I just sort of had that watershed moment of having that realization a little bit like a lightning bolt but no, I think that it is that nobody else is ever going to be your cheerleader. I think you're the one that's going to have to believe in yourself and to be able to do that and it's an incredibly hard combination because creativity's foundation is insecurity. Anytime you get a blank piece of paper or a blank screen and you make a mark on it, it's personal. Of course, it is. So, then the way you react to and think about it is different than some of those other things. That's what I said, I think, that that's the thing that I’ve discovered or I’ve learned in my journey has been the moments when I felt like I was going to share something hard or painful or embarrassing or whatever that was in the moments whenever I said it, in the moments whenever I owned it, I would get it back in support 10 times bigger than I ever imagined because then you'd get those people who'd go “Oh my God, I’ve been through that same thing. I’ve never heard anybody talk about that. I’ve never heard anybody admit that before.” And so, then all of a sudden, you would almost have this immediate support system of, again, people who would kind of come running in to help. That's what I said is, for me, it's just honesty is the key to a lot of that stuff but I think that was what I spent 38 years of my life valuing what other people thought way, way too much. And in the moments whenever I started to believe in myself, in the moments whenever I started to listen to my voice to define my brand, that was when my success really exploded and it was because then that was the point whenever I was able to drive an opinion and to really be successful.
Jayneil: My best part from that was when you said 38 years because, I got to be honest, a lot of people including me sometimes want success a little bit earlier.
Stephen: Well, sure. Don't we all? That's why I said. And, again, I think we're all burdened with that thing if you look at somebody else and go “They did it better. They did it faster.” I mean I spent you know almost half of my life struggling with that. So, that's why I said, is I think whenever people look at the state that I’m in now or what it is I’ve built or what my brand is or things like that, you can go like “Oh, he had it all figured out.” Hell, no. No, I still don't. Again, I think that's the part of it is I think we like to think that there is like an end state, there's a place where you win or you get it right or you figure it out and you don't. I mean, again, I’ve been around celebrities. Everybody is in this same place. It's just the level exposure, the name recognition that you have is the only difference. Everybody has the same insecurities. They're like nobody is kind of like “Oh, well, they found the magic formula.”
Jayneil: I think part of it is also that I feel because of social media and you see a lot of examples of people at age of 19, 20 strike it really big and then that becomes the norm and that just kind of permeates through the fabric where everybody thinks that they have to do it faster and before everybody else.
Stephen: Yeah but there's no script and I’ve always believed this. I think there is no script to what it is you do with your life. There's no script to your career. And again, I think, it's very easy to look at everybody else and, like I said, you look at their upbringing, you look at their success and it doesn't look like yours. And so, you feel less than, you feel different. No, I think that's the thing. It’s like in your life, everybody's like “Okay, yeah, you're supposed to go to college. You're supposed to get married. You have 2.5 kids. You live in the suburbs.” There's this series of events that we see over and over again in the media and in society. And if you don't do that, then somehow something is wrong.
Jayneil: Exactly.
Stephen: And that's why I said no, my wife and I’ve been married for nearly 20 years. We do not have kids. There's a lot of stuff that we do differently and it's funny to watch the social reaction of people going like “Oh, is something wrong? Is that why you don't have kids?” and it's like “No. To be honest, we both feel like we're just too selfish and we like to travel too much.” That's the thing is like there are these rules that we all seem to have agreed on. I don't understand why. I don't understand why do you have to do that series of things and the same thing in your career. As long as you find success and you are happy and, again, you're able to provide for your family and do stuff like that, who gives a shit like what other people are doing because I think that's the problem is the biggest underlying thing I would say on topics like this is I talk to so many creatives, I talk to so many leaders, so many people who are spending so much of their life trying to be who they think people want them to be that they are missing out on who they are because they think there is this script and who they are supposed to be and they are wildly, wildly unhappy because they're trying to, like I said, be this imaginary person that's not who they really are.
Jayneil: Then how does one conform with society and get their acceptance still while not following this?
Stephen: I would say why is that the goal. I do not stand on stage, I do not do my podcast, I don't do anything of my brand for other people. At the end of the day, I feel like if I show up, I think about them but my thing has never been that I’m going to do it because I want to get famous or because I want to get rich. I do it because I believe in it. I do it because it is something that I think that needs to get talked about. I’ve just been very lucky that there is an audience who believes in that. And I will argue that, I think, if you show up honestly, if you are who you genuinely are, you will find an audience and you will find success. It's whenever you try to be what everybody else wants you to be. I don't care how many followers I have on Twitter or on Instagram. Yeah, I could get a lot more if I played the game. I don't want to. That's not who I am because that's the thing. My goal is not to make everybody else happy. If I’m saying what it is I believe, if I’m putting the message out there genuinely, I believe and I think my career has proven that you will find an audience and you will find acceptance for it but it's when that equation gets reversed that I think everybody gets into problems.
Jayneil: That's amazing, Stephen. What are some books you're reading right now? Any one specific that comes to mind?
Stephen: I think there are two that I’ve read lately. One is called Forget A Mentor, Find A Sponsor, a really, really good book that I think is a different way of looking at career development. I think that's been a good one. And I’ve finally been able to find time, and we talked about it before, to finish The Messy Middle by Scott Belsky. I think Scott, every time I’m around him, every time I read his book, I’m always like “Hey, I’ve got this really figured out.” Then I see his talk or read his book and I’m like “I have so much further to go” but yeah, I think those are both really good reads.
Jayneil: That's amazing, Stephen.
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